Dallacker [1] reports the synthesis of dimethoxy-methylene-dioxy-allylbenzenes including pseudo-dillapiole (Dallacker's pseudo-dillapiole compound 8f, 4,5-dimethoxy-2,3-methylenedioxy-1-allyl-benzene) and nor pseudo-dillapiole (Dallacker's compound 8e, 6-methoxy-2,3-methylenedioxy-4-allyl-phenol). Dallacker also shows a number of position isomers of those allyl benzenes, including dillapiole (Dallacker's "Dill Apiole", 2,3-Dimethoxy-4,5-methylenedioxy-allyl-benzene), apiole (Dallacker's compound 7, 5,6-dimethoxy-2,3-methylenedioxyallyl-benzene), 2,5-dimethoxy-3,4-methylenedioxy-allyl-benzene (Dallacker's "Petersilen-Apiol"), 4,6-dimethoxy-2,3-methylene-dioxy-allyl-benzene (Dallacker's compund 4i),and 2,6-dimethoxy-3,4-methylenedioxy-allyl-benzene (Dallacker's compound 5i). Dallacker also shows monomethoxy, allyloxy, hydroxy (allyl-phenol), nitro, amino, acetamino, and propenyl derivatives.
However, these compounds of Dallacker are very dissimilar to Applicants' compounds, and he does not teach or suggest nonane/nonene substituted alkylidenedioxybenzene compounds. Further, Dallacker neither shows nor suggests any biological activity, much less antimicrobial or antifungal properties.
Several methylenedioxyphenyl compounds and the compound dillapiole 5,6-dimethoxy-3,4-methylenedioxy-1-allyl benzene, were reported by Devakumar, et al. [2], and in an Indian patent [3], No. 128,129 (1969) to have synergic activity with pyrethrum insecticides.
In the provisional specification of the Indian Pat. No. 128,129 attention was focused on the propyl analog of dillapiole because of undesirable physiological side effects of the allyl side chain. The allyl side chain was hydrogenated in the presence of a Raney-nickel catalyst, and the resulting dihydro compound was found to be an effective synergist with pyrethrins against houseflies, cockroaches and flour beetles.
Citrus Canker is a deadly plant disease caused by Xanthomonas campestris spp. This disease causes millions of dollars damage to citrus crops in the world each year, adversely affecting the world food supply. Currently, the only solution is containment by isolation/removal of the diseased plants, followed by burning the groves. A recent newspaper article (S. F. Chronicle Feb. 18, 1986, p. 17) reports that a serum of "old beer and bacteria" developed by RAM Chemical of Borger TX said to be 100% effective in stopping outbreaks of canker.
Wheat powdery mildew (WPM) is a fungal pathovar, Erysiphe graminis, that causes extensive damage to wheat crops. A variety of compounds are used to combat these diseases. For example, wheat is treated with duPont's BENOMYL, methyl 1-(butylcarbamoyl)-2-benzimidazolecarbonate, Farbenfabriken Bayer's EDIFENPHOS, O-ethyl-S,S-diphenyl-dithiophosphate, and Bayer AG/Mobay Chemical Company's BAYLETON, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-1)-2-butanone. However, the Edifenphos cannot be sold or used in the U.S., is toxic to fish, should not be mixed with alkaline materials, and cannot be used within 10 days before or after a propanil application. Benomyl is likewise toxic to fish, livestock may not be grazed on treated areas, it should not become wet during storage or combined with alkaline pesticides and apples do not express fine fruit finish. Bayleton exhibits some plant stunting and deformation on ornamentals when used at excessive rates and is toxic to fish.
There is thus a need for new compounds which are effective against such plant diseases.